


Divorce and Dating 101

by Trigger Finger (NatashaCole)



Category: Supernatural RPF
Genre: Awkwardness, F/M, Fluff
Language: English
Status: Completed
Published: 2018-09-24
Updated: 2018-09-24
Packaged: 2019-07-17 06:14:31
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 4,227
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16089734
Author URL: https://archiveofourown.org/users/NatashaCole/pseuds/Trigger%20Finger
Summary: Dating is difficult. It’s even more difficult when you’re an adult who has forgotten how to date. Reader and Rich have been carefully navigating their relationship secretly; a relationship that Rich wants to be more open with. Reader reflects on the difficulties of her divorce, her friends constant insistence on setting her up with random men, and the moment that she found what she didn’t know she was missing.





	Divorce and Dating 101

**Author's Note:**

> I had a request for a Rich x Reader with a fluffy relationship reveal.
> 
> This is my very first Rich oneshot. I’ve written him plenty, but never as a main character. Hopefully, it’s okay. It was actually really cathartic to write.
> 
> Also, for the anon who requested this; I hope you are okay. I’ve been in a very similar situation, and I know it doesn’t seem like it now, but things will get easier.

You stood backstage, listening as Rob and Rich began their introduction. The two men exchanged comments that eventually turned into an argument. You couldn’t help but laugh as you listened. They always had such a fun dynamic between them; even as Rob was now giving Rich a hard time about his long-running bachelor lifestyle. Rob addressed Stephen, who was still sitting at his drums, asking him if he and Rich were in some sort of secret single men club.

The audience laughed along, knowing that the bickering between Rob and Rich was all in good fun. They gave each other an equal amount of shit, and always laughed it off.

Right now though, you wondered how Rich was really handling it. The two of you were very much in a relationship; one that you both had decided to keep quiet for the time being since it was new and difficult for both of you to find your footing.

Rich dodged questions and comments from Rob, handling things quite well. He had always wanted to at least clue in his best friend about the two of you; but your insecurities always got the best of you, and you convinced him to keep it quiet for a little while longer.

You waited patiently as the two men continued with their set, thinking back to how difficult things had been for you during the last couple of years, and how Rich had been the one thing to actually make a difference.

* * *

_It had been a long time since you had dated. You had been married to the same man for nine years and he had nearly ruined you when he up and left you, filing for divorce before you could even talk to him about it. It had been a whirlwind for you. You never fully understood why things had changed overnight, and you never did get the closure that you felt you deserved from him. Unfortunately, you had left that marriage feeling broken and unwilling to allow your heart to love anyone ever again._

_Your friends had been amazingly supportive during your divorce. You had only been working with them for a few months when everything went to hell and your husband up and left you with no warning. Even though you stuck with your work commitments and never said anything to anyone while your separation was going on, somehow they knew something was wrong. You found it easy to vent to many of them._

_They were all so kind and supportive, but none more than Rich had been._

_Time had gone on after your divorce. Most of that time had been filled with blind dates and setups that had been organized by your married friends. They hated to see you lonely, and you understood their concerns. But, you had purposely made sure those dates had ended poorly. At the time, you just weren’t interested. You were only interested in healing your heart._

_Your only single friend, Rich, was a great companion. He was there when you went on about how you appreciated your friends efforts, but you just really didn’t want to get out there yet. At least he understood._

_“Let me tell you something,” he added after a particularly lengthy moment of complaining about dating that you made him sit through, “if you don’t tell them to stop, they won’t.”_

_“I don’t want to hurt anyone’s feelings,” you replied._

_“I know you don’t. That’s your downfall,” he smiled softly. “They think you’re lonely and sad and they believe that you will only be happy again if you find the right man. They’re going to keep trying for you if you don’t tell them to back off.”_

_“You know this?”_

_“I know this. Because they did the same thing to me when I became single.”_

_“Really?”_

_“Yeah,” he chuckled. “I literally had to tell them to stop for them to actually give up.”_

_“And you’re still single,” you pointed out. “Not that it’s a bad thing.”_

_“Yeah, I am. I dunno- maybe just waiting for the right person. Either way, I don’t want other people to choose for me.”_

_“Thank you,” you said with a smile. You moved closer to him, pulling him in for a hug. He wrapped his arms around you tightly and you relaxed into his arms. Rich gave the best hugs, and he always knew how to comfort you._

_You took his advice. During a convention when your friends sat around discussing potential dating partners for you; as if you weren’t even in the room and had no say, you finally did as Rich had suggested. You asked them to stop trying to set you up._

_“I’m perfectly okay with being by myself right now. I know you all worry and you want me to be happy; but I’m learning to be happy with myself first. I’m okay. I don’t need someone to complete me.”_

_You pleaded with them, wanting just a moment to breathe without having to worry about whether or not you would impress the next date and whether or not it even mattered._

_“You sound just like Rich,” Rob replied, giving you a confused look._

_“So?”_

_“So… he’s still single and alone.”_

_“There’s nothing wrong with being on your own,” you reminded him._

_“I know,” he mumbled. “We just worry about you.”_

_“I know you do. And I appreciate the concern. But, how about you let me decide if I’m ready to date or not? Maybe you can let me meet someone on my own.”_

* * *

_You walked back to your hotel room with Rich at the end of the con. You talked excitedly to him about how you had finally stood up for yourself to your friends. He smiled as he listened to you, seemingly impressed with how you had handled it all._

_“Right,” he began, “so now you can relax and not worry about who they’ve set you up with and whether or not you have to impress anyone. You get to just be you. Figure it all out on your own.”_

_“Yeah, it feels really good to know that I don’t have to feel obligated to date someone.”_

_“It’s a good feeling. Dating is stressful,” he chuckled as the two of you stopped in front of your room. “Take your time. Wait until you meet someone that you just know that you want to be around. Wait for someone that you actually want to get to know better.”_

_You don’t know what came over you in that moment. Maybe it was the way Rich stood there awkwardly, running his hand against the back of his neck as he started at the ground. Or, maybe it was the fact that you knew that it would be a mistake not to see if something could be there with him._

_“Do you-” you caught yourself, wondering if you were pushing things too much with him. Your curiosity got the better of you though, so you decided to go for it. “Do you want to have dinner with me?”_

_Rich looked up at you, surprised really at the mention of it._

_“Dinner? Like… with everyone, like we always do?”_

_“No. I mean, just you and I. Together.”_

_“As friends-” he said, shaking his head, “of course. I have dinner with friends all the time.”_

_“No, Rich.” You grabbed his hand in yours, giving it a squeeze when you noticed how nervous he seemed. “I want to know if you’ll go on a date with me.”_

_“Really?” He asked. He looked at you; eyes wide behind his thick frames, a small smile forming on his lips._

_“Yeah, really. I mean, we’re the only single ones here. You get me. You know what it’s like to start dating after a long relationship.”_

_“Oh, y-yeah,” he stuttered, now looking embarrassed. “Like, a practice date. Or, a ruse to keep our friends off our backs.”_

_“Oh- no!” You nearly shouted, only now realizing how you made that sound. “I mean, I like you. You’re a good man, Rich. I just figured… we get along so well and have so much in common… maybe it wouldn’t hurt to see if-” You paused again, feeling a little vulnerable at the thought of what you wanted to say. You know you meant it, but it was difficult to convey your feelings after so many years of holding them back._

_“… to see if there’s something there?” He asked hopefully._

_“Yeah,” you replied with a smile._

_“I’d really love that, Y/N.”_

_“Okay,” you smiled harder now, suddenly turning clumsy as you moved to open your hotel room door._

_“Is tonight good for you?”_

_“That’s great,” you said as you finally got your key to work. “Um, wanna pick me up in an hour? I just need to get ready.”_

_“Yes, I will do that.” He began to walk backwards, heading in the direction of his own room. He gave you some strange hand motions as he left, making you smile at how excited he seemed. “I will be right back here at your door in one hour, and we will go on a date.”_

_“Great,” you laughed. “Should I dress up?”_

_“I have no plan,” he reminded you. “This was your idea. I’ve gotta figure out where to take you. Do you usually dress up for a first date?”_

_“Yeah, I think it’s a requirement or something.”_

_“Okay, then dress up,” he insisted. “I will also dress up and I will be right back here in an hour.”_

_“Okay,” you chuckled. You could feel your face heat up as you watched him stumble slightly over the carpet of the hallway._

_“I’m just gonna… walk normal now,” he explained. You saw his own face turn red an it relaxed you a bit to know that you weren’t the only one who was nervous._

_Just as promised, Rich was knocking at your door exactly an hour after he had dropped you off. You moved to answer it, suddenly feeling a strange nervousness come over you. You knew Rich, you had no reason to be nervous around him. Another part of you realized that maybe you really liked him as a bit more than just a friend. You didn’t hold high hopes for tonight, but you sort of looked forward to getting to know him a little better; you looked forward to going on a date with someone that you actually connected with on your own terms._

_You opened the door as you took a deep breath, telling yourself to relax about tonight. It was just Rich. There was no reason to be nervous. Once you had the door open, your breath caught at the sight of him._

_He was wearing slacks and a white button up shirt with a blazer. His hair was combed back and he had decided to wear his glasses. You really adored him in glasses, it made him look so handsome, even if you had never admitted it out loud before. You breathed a sigh of relief now that you realized that you hadn’t overdone it with the whole ‘dressing up’ idea. Just as you took in the sight of him, his eyes were taking you in as well._

_“Wow, that dress…” he trailed off. You blushed suddenly, again wondering why this was such a big deal to you. You stared down at the ground, slightly flustered that he was checking you out. It had been a long time since a man had looked at you this way._

_You had decided to wear a simple little black dress tonight. It wasn’t anything too sexy, but you made sure that it hugged all your curves and gave you an excellent amount of cleavage. You had bought the dress a long time ago solely for dating purposes. You had just never worn it until now, mostly because you had been so disappointed in your dating life. For some reason, tonight felt like the right night to wear it._

_“Thank you,” you mumbled. You grabbed your handbag and made your way out of your room._

_“You ready?” Rich asked as he held out a hand to you. You nodded, hesitating for a moment before you took his hand in yours. The contact made your heart flutter, your nerves heightening._

_The actual date itself had gone better than you could have expected in the end. Truthfully, you expected it to turn into a train-wreck just as all of the other dates had. You were bad at dating, and you had a feeling that Rich wasn’t very good at it either._

_The two of you were all nerves as you had dinner together. You worried that maybe you had ruined something that had been just fine to begin with. You didn’t want for things to be weird between you and Rich, but as you sat and awkwardly ‘dated’ him that night, you got the feeling that things had become just that._

_During an unusually long pause in the conversation, Rich looked over at you as you fidgeted with your silverware._

_“Why is this so weird?” He asked._

_“I don’t know,” you replied. “Usually, you and I can talk for hours with no problem. I always feel so comfortable with you, and now I don’t.”_

_“Me neither,” he chuckled. “I don’t want for us to be like… this.”_

_“Did we make a mistake?” You asked._

_He stayed quiet for a moment before shaking his head. “No, I don’t think was a mistake. Maybe we’re just putting too much pressure on ourselves.”_

_“I hate dressing up for dates,” you blurted out. “I never wear this much makeup and my feet are killing me because I don’t wear heels.”_

_“You look beautiful,” he smiled, “no matter what you wear.”_

_“I also really don’t like fancy restaurants. I feel like everyone is judging me, and I can’t even read the damn menu.”_

_“Yeah,” he replied as he looked around. “This place is really stuffy. I’m sorry. I was just trying to impress you.”_

_“Do you think this would be less weird if we just… stopped trying to impress each other.”_

_“Maybe.”_

_“Because, I already like you,” you said quickly. “We already get along so well when we’re just ourselves.”_

_“Yeah, to be honest, I just don’t know how to act around you tonight.”_

_“And I don’t know what I’m doing,” you laughed. “I don’t know how to date. There’s nothing that teaches you how to be divorced, or how to date after divorce. I’m terrible at this and I just do what everyone else tells me I should do. But, I’m doing all of that tonight, and I feel so uncomfortable.”_

_“I don’t want to make you uncomfortable…”_

_“It’s only uncomfortable because this-” you motioned between you and Rich, “this isn’t us. This isn’t how we are with each other.”_

_Rich leaned across the table, lowering his voice to you. “Do you wanna get out of here?” He asked. “We could got to a bar nearby, have some drinks, like we do. We could just… figure it out together.”_

_“I think that is a great idea.”_

* * *

_After dinner had been eaten and the bill had been payed, Rich escorted you to a nearby bar. Neither of you had been there before, but there was at least music and a sense of ease in the air. You found a quiet table in a corner of the bar and Rich ordered drinks and brought them over. You sipped happily on your beer, feeling a lot more relaxed now that you weren’t forced to drink wine just because you thought that’s what you should do on a date. Rich enjoyed his beer as well, looking as if even he had eased up a bit._

_The two of you chatted; discussing work and just life in general. Most of what he had to share you already knew and much of what you said about yourself, he already knew._

_“Dating is weird, right?” You said, voice loud as you tried to speak over the music._

_“It is,” he agreed._

_“It’s just- weird that you and I are sitting here, pretending to try to get to know each other when we already do.”_

_“It’s more like we’re just hanging out together.”_

_“Yeah,” you smiled. “Hey, I’m sorry that it got awkward earlier. I really don’t want us to ever feel awkward with each other.”_

_“Me neither,” he replied. “Maybe we can just keep hanging out. I think when we call it a date, it freaks us both out. If we just keep it casual, maybe it will be easier.”_

_“I like that.”_

_The two of you continued to drink, this time slipping into conversation the way you normally would. When you stopped thinking of this as a date with your friend, the tension eased up and you were no longer stuck in the mindset of dating. Now, you were spending time with Rich. Just Rich. The same goofy, adorable man that you had come to know so well after all this time._

* * *

_At the end of the night, Rich walked you back to your hotel room. The two of you paused outside of the door, things turning awkward again as you tried to figure out what was supposed to happen next._

_“I had a nice time,” he said, giving you a crooked smile._

_“I really did too,” you agreed._

_“If you’re up for it, maybe we can hang out like that again sometime.”_

_“I would like that.” You reached out to him, taking his hand in yours when you noticed how uncomfortable he seemed. “Another date.”_

_“I thought we weren’t calling it a date,” he chuckled._

_“Yeah, well, I think it’s a lot less weird now that we’ve actually been on one; even if we decided not to call it that.”_

_“Okay, yeah, another date,” he smiled, his eyes sparkling as he looked at you._

_“You have my number,” you reminded him._

_“I do. And, I will call you.” He hesitated briefly, looking antsy as he stood there with his hand in yours. “To be honest, I’m not sure of what to do next. I mean, we went out… we had a good time at the end…”_

_“Yes,” you said with a laugh. You nervously tilted your head down to stare at the ground._

_“Am I supposed to kiss you goodnight?” He asked. He turned his face up into a look of concentration, as if he were thinking hard about where to take this. “Is that too much?”_

_“Um, I haven’t kissed someone in a really long time.”_

_“What? Even after all those dates you got set up on?”_

_“Well, those never worked out,” you reminded him._

_“Okay, no kissing. A hug? I really don’t know what to do.” He let out a nervous laugh, blushing as he waited for you to respond._

_“Maybe a hug is okay for now.”_

_He pursed his lips, nodding in agreement as he moved toward you. He let go of your hand, wrapping his arms around you as he drew you in for a firm hug. You moved to bring your arms around his waist, feeling your heart race now that he was holding you. You rested your face against his chest, subconsciously breathing in his scent as you closed your eyes. He smelled amazing. More importantly, you relaxed into his embrace, feeling comfort for the first time in a long time. You kept your arms tight around him for a long time. He didn’t budge and you assumed he was waiting for you to end the hug._

_When you finally decided to pull back, you glanced up at him as you kept your arms at his waist. He brought a hand up to your face, stroking his thumb against your cheek and you were certain that you were the brightest shade of red right now. You stared into each others eyes for a moment, and something came over you._

_Without really thinking about it, you tilted your face up to his, stopping just shy of his lips. His breath caught, but he didn’t stop you; so, you leaned in, pressing your lips to his. You had meant for it to be an innocent kiss. Just to see what it was like. You thought that maybe it would be just as weird as your date with him had been, you were friends after all._

_You couldn’t pull away from him though. He kept his hand at your cheek and stiffened up as he realized that you were kissing him. You were all nerves now, and so was he. It took just a few moments for the two of you to melt into it though. When you realized that it didn’t feel weird at all, you pressed harder against him. This felt… nice. He kissed you back finally, pulling your face toward his as much as he could. The innocent kiss turned fairly heated. You parted your lips for him, allowing him to kiss you deeply; which he excitedly accepted._

_When you had kissed for long enough to deprive yourselves of air, you did pull back. The second you lost that contact with him, you felt incomplete. He smiled at you, still stroking his fingers along your face and you smiled back._

_“That was an interesting turn of events,” he said._

_“I’m sorry,” you muttered. “I just… had to know.”_

_“I hope I didn’t disappoint.”_

_You shook your head in protest. “No, not at all. That was… unexpected.”_

_“Yeah, the beard takes some getting used to.”_

_“No,” you laughed. “It was unexpected the way I- I really enjoyed that.”_

_“Did you think kissing me was going to be terrible?”_

_“I just thought it would be weird. You know, since everything else tonight has been.”_

_“It wasn’t weird?”_

_“Not for me,” you said quickly. “Was it weird for you?”_

_“I honestly thought that the two of us kissing would be bad.”_

_“Me too.”_

_“But, it wasn’t bad. At all.”_

_“You know,” you began, feeling yourself blush again. “I wouldn’t mind kissing you again.”_

_He said nothing else. He simply leaned down, finding your lips with his again. You sighed against his mouth, this time feeling relaxed and natural with him. It was a bit strange that this wasn’t awkward. You had always thought of Rich as your funny friend who could always make you laugh. Right now, with the way that he was kissing you, you realized that your initial instinct of asking him out earlier had been spot on. The two of you weren’t just friends. There had always been something there, something that you had both been afraid of pursuing given the fact that you both felt so damn broken as individuals. You realized right now, that you could very easily be the people that the other needed to feel whole again._

_When the kissing ended, and you knew the two of you would have to part at least for tonight, Rich reluctantly let go of you. He slowly tried to back away, a stupid grin on his face as he watched you._

_“I’ll see you tomorrow,” you reassured him._

_“I’ll, uh, ride with you to the airport if you’d like.”_

_“I would like that,” you said. “Maybe we can sit together on the plane this time.”_

_“Really? Don’t you like to sit with Rob. He’s calming when you’re nervous.”_

_“I get the feeling I’ll be just fine with you,” you replied._

_“Okay, sounds great.” He gave you an awkward hand gesture, still trying to walk away._

_“Hey,” you called out to him. “This was good. I think this could be really good.”_

_“I really hope so.”_

_“Lets just… see where it goes.”_

_He smiled again, nodding at you before he finally turned and headed for his own room._

* * *

You were broken from your thoughts by Rob and Rich finally introducing you. You smiled as you made your way onto the stage, waving to the audience as the band played your song. You glanced over to Rich and he grinned at you, trying not to be obvious.

You offered him a smile, knowing that he had been wanting to finally be open about the two of you. These little moments on stage weren’t easy when he was being called out for being single.

Without overthinking it, you made your way to him, throwing your arms around him. He returned the embrace, sighing happily at the fact that you were being affectionate in public. He always said that he wanted people to know how lucky he was now that he had you. He wanted to be able to kiss you anytime he wanted.

You pulled back from him, looking up at him with a shy smile.

“You know, you could kiss your girlfriend now.”

He grinned harder, not arguing as he made quick work of giving a chaste kiss before you could change your mind and object.

The audience cheered for you, and Rob stared in confusion.

“Do the two of you have something you should tell me?” He asked.

Rich laughed as he looked at Rob.

“I’ll tell you all about it later, Bob-o.”

You watched as the men left the stage. Turning to face the audience, you took a deep breath. You knew you’d get questions about that, but you decided that you were ready to answer them. You were finally ready to let yourself be happy.


End file.
